How many flights depart from Wisconsin to Caribbean Islands on average per week?

As of March 2026, 239 flights take off from Wisconsin and land in Caribbean Islands each week. The most common flight departure day for this route is Sat, with 19% of weekly flights taking off on this day.

What is the cheapest airline that flies from Wisconsin to Caribbean Islands?

United Airlines, Southwest, and Spirit Airlines are the most popular carriers operating from Wisconsin to Caribbean Islands

How many flights depart from Wisconsin to Caribbean Islands on average per day?

As of March 2026, there are 34 flights per day flying from Wisconsin to Caribbean Islands. The most common time of day flights depart is 8:00AM, with 100% of flights taking off at noon.

How long is the flight from Wisconsin to Caribbean Islands?

The flight from Wisconsin to Caribbean Islands depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Milwaukee (a popular airport in Wisconsin) to Copenhagen (the most popular airport in Caribbean Islands), then the flight time is 16h 45m on average. If you fly from Madison (another popular airport in Wisconsin) to Copenhagen, then the average flight time is 20h 05m.

What airlines fly to Caribbean Islands?

American Airlines, Delta and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Wisconsin according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

Prices for flights from Wisconsin to Caribbean Islands refresh daily.

How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

As of March 2026, there are 12 operators available to choose from for flights from Wisconsin to Caribbean Islands.

How old do you have to be to fly from Wisconsin to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$88 Cheap Flights from Wisconsin to Caribbean Islands in 2026

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Find the cheapest flights from Wisconsin to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:05 am - 6:55 pm

ORD

SJU

12h 50m

1 stop

4:34 pm - 8:49 pm

SJU

ORD

5h 15mnonstop

$202Spirit Airlines

Mon, Apr 13 - Fri, Apr 17

7:17 am - 6:55 pm

ORD

SJU

10h 38m

1 stop

3:23 pm - 10:39 pm

SJU

ORD

8h 16m

1 stop

$203Multiple Airlines

Mon, Apr 13 - Fri, Apr 17

4:21 pm - 12:02 am

ORD

SJU

6h 41m

1 stop

1:29 am - 5:45 am

SJU

ORD

5h 16mnonstop

$205Multiple Airlines

Wed, Apr 8 - Mon, Apr 13

4:34 pm - 12:52 am

ORD

SJU

7h 18m

1 stop

3:23 pm - 10:39 pm

SJU

ORD

8h 16m

1 stop

$206Frontier

Tue, Apr 7 - Fri, Apr 17

6:04 pm - 9:54 am

ORD

SJU

14h 50m

1 stop

11:30 am - 11:59 pm

SJU

ORD

13h 29m

1 stop

$207Frontier

Fri, Apr 17 - Thu, Apr 23

11:55 am - 12:25 am

ORD

SJU

11h 30m

1 stop

1:29 am - 5:45 am

SJU

ORD

5h 16mnonstop

$208Multiple Airlines

Fri, Apr 10 - Mon, Apr 13

12:43 pm - 10:17 pm

MKE

SJU

8h 34m

1 stop

1:14 pm - 11:53 pm

SJU

MKE

11h 39m

1 stop

$288Delta

Tue, May 19 - Fri, May 29

5:10 am - 4:30 pm

MKE

SJU

10h 20m

1 stop

6:50 am - 7:10 pm

SJU

MKE

13h 20m

1 stop

$301Southwest

Sun, May 17 - Fri, May 22

8:05 am - 12:13 pm

ORD

MBJ

4h 08mnonstop

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

$318American Airlines

Mon, May 4 - Fri, May 8

5:00 am - 3:37 pm

ORD

MBJ

10h 37m

1 stop

1:15 pm - 5:55 pm

MBJ

ORD

4h 40mnonstop

$322American Airlines

Mon, May 4 - Fri, May 8

Spirit Airlines flights from Wisconsin to Caribbean Islands

Our best Spirit Airlines deals on Wisconsin to Caribbean Islands flight tickets

Spirit Airlines

Apr 13

ORD5:05 amChicago O'Hare Intl

12h 50m

1 stop

SJU6:55 pmSan Juan Luis Munoz Marin Intl

Apr 17

SJU4:34 pmSan Juan Luis Munoz Marin Intl

5h 15m

ORD8:49 pmChicago O'Hare Intl

$202

Spirit Airlines

Apr 7

ORD10:55 amChicago O'Hare Intl

12h 03m

1 stop

SJU11:58 pmSan Juan Luis Munoz Marin Intl

Apr 13

SJU1:29 amSan Juan Luis Munoz Marin Intl

5h 16m

ORD5:45 amChicago O'Hare Intl

$212

Spirit Airlines

Apr 7

ORD10:55 amChicago O'Hare Intl

12h 03m

1 stop

SJU11:58 pmSan Juan Luis Munoz Marin Intl

Apr 15

SJU10:59 amSan Juan Luis Munoz Marin Intl

5h 09m

ORD3:08 pmChicago O'Hare Intl

$217

Delta flights from Wisconsin to Caribbean Islands

Our best Delta deals on Wisconsin to Caribbean Islands flight tickets

Delta

May 19

MKE12:43 pmMilwaukee-Mitchell

8h 34m

1 stop

SJU10:17 pmSan Juan Luis Munoz Marin Intl

May 28

SJU5:43 pmSan Juan Luis Munoz Marin Intl

7h 10m

1 stop

MKE11:53 pmMilwaukee-Mitchell

$288

Delta

Apr 25

MKE2:50 pmMilwaukee-Mitchell

7h 22m

1 stop

SJU11:12 pmSan Juan Luis Munoz Marin Intl

May 1

SJU6:15 amSan Juan Luis Munoz Marin Intl

10h 03m

1 stop

MKE3:18 pmMilwaukee-Mitchell

$317

Delta

Apr 25

MKE2:50 pmMilwaukee-Mitchell

7h 22m

1 stop

SJU11:12 pmSan Juan Luis Munoz Marin Intl

May 5

SJU5:34 pmSan Juan Luis Munoz Marin Intl

7h 23m

1 stop

MKE11:57 pmMilwaukee-Mitchell

$326

momondo Fare Finder

Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/13

5:05 am-6:55 pm

1 stop12h 50m

San Juan Luis Munoz Marin Intl

Fri 4/17

4:34 pm-8:49 pm

Nonstop5h 15m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 4/13

7:17 am-6:55 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:39 pm

1 stop8h 16m

$203

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 4/8

4:21 pm-12:02 am

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 4/7

4:34 pm-12:52 am

1 stop7h 18m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:23 pm-10:39 pm

1 stop8h 16m

$206

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/17

6:04 pm-9:54 am

1 stop14h 50m

San Juan Luis Munoz Marin Intl

Thu 4/23

11:30 am-11:59 pm

1 stop13h 29m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 4/10

11:55 am-12:25 am

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Mon 4/13

1:29 am-5:45 am

Nonstop5h 16m

$208

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 5/19

12:43 pm-10:17 pm

1 stop8h 34m

San Juan Luis Munoz Marin Intl

Fri 5/29

1:14 pm-11:53 pm

1 stop11h 39m

$288

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 5/17

5:10 am-4:30 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Fri 5/22

6:50 am-7:10 pm

1 stop13h 20m

$301

Quickest round-trip

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

8:05 am-12:13 pm

Nonstop4h 08m

Montego Bay Sangster Intl

Fri 5/8

1:15 pm-5:55 pm

Nonstop4h 40m

$318

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 5/4

5:00 am-3:37 pm

1 stop10h 37m

Montego Bay Sangster Intl

Fri 5/8

1:15 pm-5:55 pm

Nonstop4h 40m

$322

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $315. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $317.

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Punta Cana for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $444 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Wisconsin for as low as $334 on momondo.

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Fastest flight time	3h 24m
Direct flights	Every day
Airports in Caribbean Islands	99 airports

The fastest flight from Wisconsin to Caribbean Islands takes 3h 24m

Direct flights go from Wisconsin to Caribbean Islands every day.

There are 99 airports in Caribbean Islands. From Wisconsin there are direct flights to Nassau Intl (NAS).

Search flight deals

When did momondo last update prices for flights from Wisconsin to Caribbean Islands?
Prices for flights from Wisconsin to Caribbean Islands refresh daily.
How many operators does momondo search for flights from Wisconsin to Caribbean Islands?
As of March 2026, there are 12 operators available to choose from for flights from Wisconsin to Caribbean Islands.
How old do you have to be to fly from Wisconsin to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Wisconsin to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Wisconsin to Caribbean Islands is Airbus A320-100/200 (32.00% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (15.08%), Boeing 737-800 Passenger/BBJ2 (winglets) (8.76%), and Boeing 737-800 (6.93%).

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $112	Free Cancellation	Rating 7.9 8,318 reviews	Search Delta flights
Frontier	PriceFrom $156	Free Cancellation	Rating 5.7 3,020 reviews	Search Frontier flights
United Airlines	PriceFrom $202	Free Cancellation	Rating 7.4 9,464 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $208	Free Cancellation	Rating 6.3 8,538 reviews	Search Spirit Airlines flights
American Airlines	PriceFrom $215	Free Cancellation	Rating 7.1 11,487 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest flights
Sun Country Air	PriceFrom $547	Free Cancellation	Rating 6.8 340 reviews	Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.